Sodium Hydroxide → HCID 11486771, compound

HRID 1267448Notes

Reaction equation

HRID 1267448 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][CH:14]2[CH2:19][CH2:20][CH:21]([OH:30])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH:21]([OH:30])[CH2:20][CH2:19][CH:14]2[CH2:15][CH2:16][C:17](=[O:18])[N:13]2[CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][CH:6]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69270428HCID 69270428, compound

Product 1

HCID 11486771HCID 11486771, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogous to the procedure described for Example 1A, Step F, 4-(3-{2-[4-(4-fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (61.1 mg, 0.143 mmol) was hydrolyzed with 6N NaOH (1 mL) in MeOH (5 mL) at room temperature over 24 h. Purification by medium pressure chromatography eluting with a solvent gradient (CH2Cl2to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2) provided the title compound (45 mg). 1H NMR (CDCl3) δ7.97 (d, 2H), 7.25 (m, 2H), 7.14 (m, 2H), 6.99 (m, 2H), 3.75-3.58 (m, 3H), 2.97 (m, 1H), 2.69 (m, 4H), 2.40 (m, 2H), 2.15-1.35 (m, 9H); MS 413.8 (M+).

Workup

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (CH2Cl2to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4a82f00f083d49d2a139af9ff0d5d04a
Source dataset
uspto-grants-2003_04
Patent number
US06552067B2

Reaction notes

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